[(2R,3S,4S,5R,6R)-2-bromo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate | 125608-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3S,4S,5R,6R)-2-bromo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 125608-47-1
• 化学式: C₃₄H₃₃BrO₆
• 分子量: 617.536
• InChiKey: WYNGNJVOGUHOIP-ZPZOKNLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 、 [(2R,3S,4S,5R,6R)-2-bromo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.33h， 以1.052 g的产率得到ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside
  参考文献：
  名称：

  Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO₄

  摘要：

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.

  DOI：

  10.1021/jo0508595
• 作为产物：
  描述：

  (2S,3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran 在 溴 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到[(2R,3S,4S,5R,6R)-2-bromo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
  参考文献：
  名称：

  将戊4烯基糖苷转化为糖基溴化物

  摘要：

  已开发了用于化学特异（a）保护和（b）异头中心活化的戊4烯基糖苷的独特特征，以在不影响可氧化和酸敏感保护基的温和条件下制备糖基溴化物。收率极高，因此该产品可就地用于糖偶联。

  DOI：

  10.1039/c39890001124

文献信息

• Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 5. n-Pentenyl Ortho Esters for Mannan Components
  作者：Carmichael Roberts、Robert Madsen、Bert Fraser-Reid

  DOI：10.1021/ja00110a010

  日期：1995.2

  Procedures for rapid assembly of multigram amounts of mannan components have been examined. Although these studies are reported in the context of the mannan moiety of the glycan anchors of membrane-bound glycoproteins, the procedures should be applicable to the wider family of mannose-containing glycoproteins. Readily prepared n-pentenyl ortho esters of mannose are shown to be versatile substrates that can serve as glycosyl donors in their own right or be used to furnish mannosyl bromides or n-pentenyl alpha-D-mannosides. Thus three glycosyl donors of different reactivities and stabilities are obtainable from the same precursor, all three being activated under mild conditions. Two approaches are described. in the first, a portion of the starting n-pentenyl ortho ester is converted into an n-pentenyl glycoside (NPG) by acid-catalyzed rearrangement, while another portion is titrated with bromine to give a glycosyl bromide. These are coupled under Koenigs-Knorr conditions to give an n-pentenyl disaccharide which is then processed to become a glycosyl acceptor. A third portion of the ortho ester, after suitable protecting group adjustments, is also titrated with bromine and coupled to the disaccharide acceptor to give the desired trimannan. The instability of glycosyl bromides detracts from this route, and so a second approach which avoids their use completely was pursued in which NPG obtained from the acid-catalyzed rearrangement was converted into a vicinal dibromide. The latter is then able to serve as a glycosyl acceptor for coupling to a donor obtainable by reaction of the n-pentenyl ortho ester with halonium ion. The dibromopentanyl disaccharide produced then becomes an acceptor for a donor derived from n-pentenyl mannoside. The second approach uses no unstable reactants, is therefore experimentally less demanding, and can be operated conveniently on a large scale.
• A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein
  作者：Uko E. Udodong、Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/ja00070a048

  日期：1993.8
• KONRADSSON, PETER;FRASER-REID, BERT, J. CHEM. SOC. CHEM. COMMUN.,(1989) N6, C. 1124-1125
  作者：KONRADSSON, PETER、FRASER-REID, BERT

  DOI：——

  日期：——